Nucleophilic Aromatic Substitution (SNAr) as an Approach to Challenging Carbohydrate-Aryl Ethers

Alexander S Henderson; Sandra Medina; John F Bower; M Carmen Galan

doi:10.1021/acs.orglett.5b02413

Nucleophilic Aromatic Substitution (SNAr) as an Approach to Challenging Carbohydrate-Aryl Ethers

Alexander S Henderson, Sandra Medina, John F Bower, M Carmen Galan

School of Chemistry

Research output: Contribution to journal › Article (Academic Journal) › peer-review

65 Citations (Scopus)

Abstract

A general and practical route to carbohydrate-aryl ethers by nucleophilic aromatic substitution (SNAr) is reported. Upon treatment with KHMDS, C-O bond formation occurs between carbohydrate alcohols and a diverse range of fluorinated (hetero)aromatics to provide the targets in good to excellent yields. Commercially available arylating agents, high atom economy, and high regioselectivity are notable features of the protocol. The aryl ether products have potential for wide-ranging applications as exemplified by the synthesis of a novel chiral P,N-ligand.

Original language	English
Pages (from-to)	4846-4849
Number of pages	4
Journal	Organic Letters
Volume	17
Issue number	19
Early online date	17 Sept 2015
DOIs	https://doi.org/10.1021/acs.orglett.5b02413
Publication status	Published - 2 Oct 2015

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GLYCO-TOOLS: Bio-Inspire Tools for Glycoscience - ERC
Galan, M. C. (Principal Investigator)
1/07/15 → 31/12/20
Project: Research
Catalytic stereoselective synthesis of glycosides
Galan, M. C. (Principal Investigator)
1/07/13 → 1/07/15
Project: Research
3-month Core Capability for Chemistry Research
Crosby, J. (Principal Investigator)
1/01/13 → 1/04/13
Project: Research

Cite this

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title = "Nucleophilic Aromatic Substitution (SNAr) as an Approach to Challenging Carbohydrate-Aryl Ethers",

abstract = "A general and practical route to carbohydrate-aryl ethers by nucleophilic aromatic substitution (SNAr) is reported. Upon treatment with KHMDS, C-O bond formation occurs between carbohydrate alcohols and a diverse range of fluorinated (hetero)aromatics to provide the targets in good to excellent yields. Commercially available arylating agents, high atom economy, and high regioselectivity are notable features of the protocol. The aryl ether products have potential for wide-ranging applications as exemplified by the synthesis of a novel chiral P,N-ligand.",

author = "Henderson, {Alexander S} and Sandra Medina and Bower, {John F} and Galan, {M Carmen}",

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T1 - Nucleophilic Aromatic Substitution (SNAr) as an Approach to Challenging Carbohydrate-Aryl Ethers

AU - Henderson, Alexander S

AU - Medina, Sandra

AU - Bower, John F

AU - Galan, M Carmen

PY - 2015/10/2

Y1 - 2015/10/2

N2 - A general and practical route to carbohydrate-aryl ethers by nucleophilic aromatic substitution (SNAr) is reported. Upon treatment with KHMDS, C-O bond formation occurs between carbohydrate alcohols and a diverse range of fluorinated (hetero)aromatics to provide the targets in good to excellent yields. Commercially available arylating agents, high atom economy, and high regioselectivity are notable features of the protocol. The aryl ether products have potential for wide-ranging applications as exemplified by the synthesis of a novel chiral P,N-ligand.

AB - A general and practical route to carbohydrate-aryl ethers by nucleophilic aromatic substitution (SNAr) is reported. Upon treatment with KHMDS, C-O bond formation occurs between carbohydrate alcohols and a diverse range of fluorinated (hetero)aromatics to provide the targets in good to excellent yields. Commercially available arylating agents, high atom economy, and high regioselectivity are notable features of the protocol. The aryl ether products have potential for wide-ranging applications as exemplified by the synthesis of a novel chiral P,N-ligand.

U2 - 10.1021/acs.orglett.5b02413

DO - 10.1021/acs.orglett.5b02413

M3 - Article (Academic Journal)

C2 - 26379123

SN - 1523-7060

VL - 17

SP - 4846

EP - 4849

JO - Organic Letters

JF - Organic Letters

IS - 19

ER -

Nucleophilic Aromatic Substitution (SNAr) as an Approach to Challenging Carbohydrate-Aryl Ethers

Abstract

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Projects

GLYCO-TOOLS: Bio-Inspire Tools for Glycoscience - ERC

Catalytic stereoselective synthesis of glycosides

3-month Core Capability for Chemistry Research

Cite this